Chain or cyclic epoxy compounds, esters and lactones are important compounds as pharmaceuticals, perfumes, dyes, organic intermediates and materials for polymeric resins.
Epoxy compounds and esters or lactones are, even though they are different in reaction materials, common in that they are produced by oxidation reaction using perbenzoic acid, peracetic acid, trifluoroperacetic acid or another peracid. For example, an epoxy compound is produced by the reaction of an alkene, a cycloalkane or another compound having a non-aromatic ethylenic bond with the peracid. An ester or lactone is obtained by the reaction of a chain or cyclic ketone with the peracid, i.e., by a so-called Baeyer-Villiger rearrangement (oxidation). The peracid is, however, unstable and should be handled with extreme caution. In addition, an equivalent amount of a carboxylic acid is by-produced in the reaction using the peracid.
As a production process for epoxy compounds is known a process of allowing a hypohalogenous acid to act on an unsaturated compound to give a halohydrin, and treating the halohydrin with an alkali. This process is, however, unable to be applied to olefins each having a complicated structure. Furthermore, there is known a process of allowing a microorganism to act on an unsaturated compound in the presence of oxygen to give a corresponding epoxy compound. Such a process using a microorganism is, however, disadvantageous in productivity, because the concentration of a substrate cannot generally be increased.
Japanese Unexamined Patent Publication No. 9-327626 discloses a process of oxidizing an unsaturated chain hydrocarbon or an alkene, cyclohexanone or cyclohexanol by molecular oxygen in the presence of an imide compound. According to this literature, however, an unsaturated chain hydrocarbon or an alkene predominantly gives a ketone or an alcohol in which the adjacent position to a double bond is oxidized, and a corresponding epoxy compound is not obtained. Cyclohexanone or cyclohexanol predominantly gives a corresponding dicarboxylic acid, but no corresponding ester or lactone.